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Sodium Bicarbonate → 5-Chloro-2-methyl-2,3,3a,12b-tetrahydrodibenzo(2,3:6,7)oxepino(4,5-c)pyrrole

HRID 63779
Notes
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Reaction equation

HRID 63779 reaction equation
[CH3:1][N:2]1[CH2:19][CH:18]2[CH:4]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=3[O:11][C:12]3[CH:13]=[CH:14][C:15]([Cl:20])=[CH:16][C:17]=32)[CH2:3]1.C(/C(O)=O)=C/C(O)=O.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH3:1][N:2]1[CH2:19][CH:18]2[CH:4]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=3[O:11][C:12]3[CH:13]=[CH:14][C:15]([Cl:20])=[CH:16][C:17]=32)[CH2:3]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 119542935-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole maleate

Product 1

HCID 99039705-Chloro-2-methyl-2,3,3a,12b-tetrahydrodibenzo(2,3:6,7)oxepino(4,5-c)pyrroleYield 103.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

0.69 Kg of asenapine maleate (1.69 moles) with a purity of 98% (HPLC) is loaded into a reactor. Toluene (7.2 L) is added, and the suspension is stirred at 25° C. A 9% solution of sodium bicarbonate (7.2 L) is added by dripping. The solution is left under stirring at 25° C. for 30 minutes. The lower aqueous phase is eliminated. The organic phase is washed with water (2×3.6 L). The solvent is evaporated under vacuum, obtaining asenapine base (0.50 Kg) in the form of oil. 4.6 L of ethanol is added. The solution is stirred, heating to 50° C. An 85% solution of phosphoric acid (0.12 L, 1.69 moles) in ethanol (0.68 L) is dripped into the solution of asenapine base at 50° C. in 10 minutes. The solution is stirred for 30 minutes at 50° C. The solution is cooled to 25° C. in approx. 2 hours. The solution is left under stirring at 25° C. for 2 hours. The product is isolated by filtration, washing with ethanol (0.75 L). The product is dried under vacuum at 25° C. for 20 hours. 0.614 Kg of asenapine phosphate is obtained (yield=94.0%). Purity >99.5% (HPLC).

Workup

  1. waitThe solution is left
  2. stirringunder stirring at 25° C. for 30 minutes
  3. washThe organic phase is washed with water (2×3.6 L)
  4. customThe solvent is evaporated under vacuum

Sources & evidence

ORD record
ord-3cfc33b6c96845d0aabb65557ffcab39
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09447109B2

Reaction notes

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